The talk explores the historical evolution of transportation modes and technologies. It traces how systems are innovated, planned and adapted, deployed and expanded, and reach maturity, where they may either be maintained in a polished obsolesce often propped up by subsidies, be displaced by competitors, or be reorganized and renewed. An array of examples supports the idea that modern policies are built from past experiences. The planning (and control) of nonlinear, unstable processes is today's central transportation problem, and that this is universal and true of all modes.